Sodium hydride → Methyl 6-chloro-3-(2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)-2-methylbenzoate

HRID 650907Notes

Reaction equation

HRID 650907 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:12])[C:5]([N:13]=[C:14]=[O:15])=[CH:4][CH:3]=1.[H-].[Na+].[NH2:18][C:19]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:21]([O-])=[O:22]>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:12])[C:5]([N:13]2[C:21](=[O:22])[CH:20]=[C:19]([C:24]([F:27])([F:26])[F:25])[NH:18][C:14]2=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21710153Methyl 6-chloro-3-isocyanato-2-methylbenzoateHCID 734469833-Amino-4,4,4-trifluoro-2-butenoate

Product 1

HCID 21710140Methyl 6-chloro-3-(2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)-2-methylbenzoateYield 58.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was prepared in a manner analogous to the second part of Step D, Example 1. Here, 16.7 grams (0.074 mole) of methyl 6-chloro-3-isocyanato-2-methylbenzoate was combined with 4.4 grams (0.110 mole) of 60% sodium hydride and 14.2 grams (0.076 mole) of 3-amino-4,4,4-trifluoro-2-butenoate in 600 mL of THF. The reaction product was purified by column chromatography on silica using a 1:1 mixture of EtOAc and hexane as eluant. The fractions containing product were combined and concentrated under reduced pressure, yielding 15.8 grams of subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to the second part of Step D, Example 1
  2. customThe reaction product was purified by column chromatography on silica using
  3. additiona 1:1 mixture of EtOAc and hexane as eluant
  4. additionThe fractions containing product
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-16ad04a994b54b608241912aceb911c0
Source dataset
uspto-grants-2001_08
Patent number
US06277847B1

Reaction notes

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